CN1041205C - 天冬酰苯丙氨酸甲酯(糖精)结晶的工艺方法 - Google Patents
天冬酰苯丙氨酸甲酯(糖精)结晶的工艺方法 Download PDFInfo
- Publication number
- CN1041205C CN1041205C CN93116206A CN93116206A CN1041205C CN 1041205 C CN1041205 C CN 1041205C CN 93116206 A CN93116206 A CN 93116206A CN 93116206 A CN93116206 A CN 93116206A CN 1041205 C CN1041205 C CN 1041205C
- Authority
- CN
- China
- Prior art keywords
- solution
- asccharin
- crystallization
- temperature
- under
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000002425 crystallisation Methods 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 38
- 108010011485 Aspartame Proteins 0.000 title claims abstract description 6
- 239000000605 aspartame Substances 0.000 title claims abstract description 6
- 235000010357 aspartame Nutrition 0.000 title claims abstract description 6
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 title claims abstract description 6
- 229960003438 aspartame Drugs 0.000 title claims abstract description 6
- 239000000243 solution Substances 0.000 claims abstract description 61
- 239000007864 aqueous solution Substances 0.000 claims abstract description 15
- 230000003472 neutralizing effect Effects 0.000 claims abstract 2
- 230000008025 crystallization Effects 0.000 claims description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000003513 alkali Substances 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- 230000007935 neutral effect Effects 0.000 claims description 13
- 238000006386 neutralization reaction Methods 0.000 claims description 10
- 238000013019 agitation Methods 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000010907 mechanical stirring Methods 0.000 claims description 5
- 238000003672 processing method Methods 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 238000000265 homogenisation Methods 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 239000002002 slurry Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 239000012065 filter cake Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 241000209094 Oryza Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000020965 cold beverage Nutrition 0.000 description 1
- 150000001875 compounds Chemical group 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL9201408A NL9201408A (nl) | 1992-08-05 | 1992-08-05 | Werkwijze voor het kristalliseren van aspartaam. |
| NL9201408 | 1992-08-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1092429A CN1092429A (zh) | 1994-09-21 |
| CN1041205C true CN1041205C (zh) | 1998-12-16 |
Family
ID=19861149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93116206A Expired - Fee Related CN1041205C (zh) | 1992-08-05 | 1993-08-04 | 天冬酰苯丙氨酸甲酯(糖精)结晶的工艺方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5502238A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0582351B1 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100294280B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1041205C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE175208T1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69322820T2 (cg-RX-API-DMAC7.html) |
| MX (1) | MX9304719A (cg-RX-API-DMAC7.html) |
| NL (1) | NL9201408A (cg-RX-API-DMAC7.html) |
| RU (1) | RU2112771C1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW321631B (cg-RX-API-DMAC7.html) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL108907A0 (en) * | 1994-03-09 | 1994-06-24 | Yissum Res Dev Co | Aspartame and process for the preparation thereof |
| EP0733641A1 (en) * | 1995-03-20 | 1996-09-25 | Holland Sweetener Company V.O.F. | Method for crystallizing alpha-l-aspartyl-l-phenylalanine methyl ester |
| CA2172022A1 (en) * | 1995-03-20 | 1996-09-21 | Tsugio Murakami | Method for crystallizing alpha-l-aspartyl-l-phenylalanine methyl ester |
| ES2273501T3 (es) * | 1998-06-30 | 2007-05-01 | Novo Nordisk A/S | Cristales de germinacion para la preparacion de peptidos o proteinas. |
| RU2205188C2 (ru) | 1998-06-30 | 2003-05-27 | Ново Нордиск А/С | Затравочные кристаллы для получения пептидов или протеинов |
| KR20000009984A (ko) * | 1998-07-29 | 2000-02-15 | 고두모 | 알파-엘-아스파틸-엘-페닐알라닌 메틸 에스테르의 결정화 방법 |
| AU1832500A (en) * | 1998-11-25 | 2000-06-19 | Nutrasweet Company, The | Purification of N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester via crystallization |
| US6281380B1 (en) * | 2000-05-18 | 2001-08-28 | The Nutra Sweet Company | Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol |
| JP2003159026A (ja) * | 2001-11-22 | 2003-06-03 | Ajinomoto Co Inc | 安定なアスパルテームスラリーの製造方法及び判定方法 |
| CN107868117B (zh) * | 2016-09-28 | 2021-04-23 | 中国科学院苏州纳米技术与纳米仿生研究所 | 司坦唑醇糖精盐及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE810577L (en) * | 1983-05-31 | 1982-09-16 | Prendergast Angela | Apparatus for fermentation |
| JPS58177952A (ja) * | 1982-04-12 | 1983-10-18 | Ajinomoto Co Inc | Ｌ−α−アスパルチル−Ｌ−フエニルアラニンメチルエステルの晶析法 |
| GB2140805B (en) * | 1983-05-31 | 1986-08-13 | Erba Farmitalia | Isolation of aspartame |
| JP2970107B2 (ja) * | 1991-05-23 | 1999-11-02 | 味の素株式会社 | α−Ｌ−アスパルチル−Ｌ−フェニルアラニンメチルエステルの製造方法 |
| JP2927070B2 (ja) * | 1991-05-23 | 1999-07-28 | 味の素株式会社 | α−Ｌ−アスパルチル−Ｌ−フェニルアラニンメチルエステルの製造方法 |
-
1992
- 1992-08-05 NL NL9201408A patent/NL9201408A/nl not_active Application Discontinuation
-
1993
- 1993-07-06 TW TW082105376A patent/TW321631B/zh active
- 1993-08-02 EP EP93202282A patent/EP0582351B1/en not_active Expired - Lifetime
- 1993-08-02 AT AT93202282T patent/ATE175208T1/de not_active IP Right Cessation
- 1993-08-02 DE DE69322820T patent/DE69322820T2/de not_active Expired - Fee Related
- 1993-08-04 CN CN93116206A patent/CN1041205C/zh not_active Expired - Fee Related
- 1993-08-04 RU RU93043868A patent/RU2112771C1/ru not_active IP Right Cessation
- 1993-08-04 MX MX9304719A patent/MX9304719A/es not_active IP Right Cessation
- 1993-08-04 KR KR1019930015085A patent/KR100294280B1/ko not_active Expired - Fee Related
-
1995
- 1995-03-01 US US08/396,861 patent/US5502238A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE69322820T2 (de) | 1999-08-19 |
| NL9201408A (nl) | 1994-03-01 |
| CN1092429A (zh) | 1994-09-21 |
| ATE175208T1 (de) | 1999-01-15 |
| MX9304719A (es) | 1994-05-31 |
| KR100294280B1 (ko) | 2001-09-17 |
| RU2112771C1 (ru) | 1998-06-10 |
| US5502238A (en) | 1996-03-26 |
| TW321631B (cg-RX-API-DMAC7.html) | 1997-12-01 |
| DE69322820D1 (de) | 1999-02-11 |
| EP0582351B1 (en) | 1998-12-30 |
| EP0582351A1 (en) | 1994-02-09 |
| KR940005552A (ko) | 1994-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |